🇺🇸 United States · The South / Southeast
Key West is the southernmost island of the Florida Keys and the southernmost point of the continental United States: from here, Havana is closer than Miami. It is a place with a spirit all its own, relaxed and bohemian, with conch-style (Caribbean) wooden houses, tree-lined streets, roosters running loose, sunsets celebrated as a ritual and a tolerant, festive atmosphere that has made it famous.
The island holds a rich history: it was a port of fishermen and shipwreck salvagers, a center of the cigar industry and a refuge for writers and artists. Ernest Hemingway lived here, and his house with its famous six-toed cats is a must. The bustle is concentrated in Old Town, around Duval Street, packed with bars, restaurants and shops, while the sea invites you to dive, fish and take boat trips across turquoise water.
This guide covers the essentials of Key West with a practical eye: the famous southernmost point marker, Hemingway's house, the sunsets at Mallory Square, Duval Street, the water activities and how to get there along the spectacular Overseas Highway. Whether for its literary history, its sunsets or its laid-back Caribbean atmosphere, Key West is a destination you fall in love with.
Key West was inhabited by Indigenous peoples and sighted by Spanish explorers, who called it Cayo Hueso ('bone island'), from which its current name derives. In the 19th century it grew prosperous thanks to the salvaging of shipwrecks (wrecking) on the reefs and, later, to the cigar industry and sponge fishing, becoming the richest city in Florida. In the 20th century it was linked to the mainland first by a railroad and then by the Overseas Highway. It drew writers like Hemingway and turned into a tourist destination and a bohemian refuge. The full story is on our history page.
Read the full history ↓The 'sunshine state': the land with the oldest European roots in the country, with St. Augustine; home of the Timucua, the Seminoles and the Everglades, of the tourism of Miami and Orlando, of Cape Canaveral and of a vibrant Latino culture.
Read the history of Florida →No exact prices: a scale from $ (budget) to $$$$$ (luxury), with 2-3 options per category.
Origins, formation and what the sources say.
The island we call Key West today was inhabited by Indigenous peoples of Florida, such as the Calusa and the Tequesta, long before the Europeans arrived. When Spanish explorers ran along the chain of keys in the 16th century, they named the southernmost island Cayo Hueso, that is, 'bone island', by tradition because they found human remains on it, possibly from old burials or from battles between tribes. From that Spanish expression comes, by phonetic adaptation, the present English name 'Key West'.
Through the colonial centuries the island stayed practically uninhabited by settlers, though it was known to sailors and fishermen. Florida was Spanish territory until 1821, when it passed to the United States. Shortly afterward, in 1822, an American businessman, John W. Simonton, bought the island, and the U.S. Navy took possession of it for its strategic value: Key West controlled the passage between the Gulf of Mexico and the Atlantic, one of the busiest sea routes of the era.
The official founding of the modern settlement dates to the 1820s. Its strategic position, at the gateway to the Straits of Florida and near Cuba, would shape its entire history, turning it into a military and commercial enclave and, in time, into one of the most singular places in the country.
Through the 19th century, Key West lived a period of remarkable prosperity thanks to a peculiar industry: wrecking, the salvaging of shipwrecked vessels. The treacherous reefs surrounding the Keys caused numerous wrecks, and the island's inhabitants specialized in rescuing grounded ships and recovering their cargo, a legal and highly lucrative activity that, so the story goes, made Key West the city with the highest per capita income in the United States in the mid-19th century.
Other industries added to that wealth. From the 1860s and 1870s on, Cuban tobacco workers arrived and set up cigar factories, turning Key West into a major center of Havana-cigar production (before many of those factories moved to Tampa). The island also prospered on sea-sponge fishing, another key part of its economy. The population grew with a mix of Bahamians, Cubans, Americans and others, which gave the island its cosmopolitan, Caribbean character.
The building of lighthouses —like the current Key West Lighthouse, rebuilt in 1848 after a hurricane— improved the safety of navigation and, paradoxically, gradually reduced the wrecks and, with them, the era of wrecking. Even so, Key West remained a prosperous port and the largest city in Florida for a good part of the 19th century, with splendid conch-style wooden houses that still define the look of its Old Town.
At the start of the 20th century, the magnate Henry Flagler took on a colossal project: extending his Florida East Coast railroad all the way to Key West, hopping from key to key over the sea. The 'Overseas Railroad' was completed in 1912 and linked the island to the mainland for the first time, an engineering feat considered the eighth wonder of the world in its day. The devastating Labor Day hurricane of 1935 destroyed much of the railroad; the present Overseas Highway (US-1), the road that today links the Keys through a succession of bridges, was later built along its route.
In the 1920s and 1930s, Key West drew writers and artists seduced by its light, its isolation and its unique atmosphere. The most famous was Ernest Hemingway, who lived there in the 1930s in the house that is a museum today, where he wrote part of his work and whose polydactyl feline descendants still inhabit the place. Other writers passed through the island as well, cementing its reputation as a creative refuge. The Great Depression hit Key West hard —the city went so far as to declare municipal bankruptcy in 1934— and the federal government, through the New Deal, actively promoted tourism as a strategy for economic recovery, laying the foundations of the industry that sustains the island today.
Through the 20th century, Key West reinvented itself as a tourist mecca, keeping its independent, tolerant and festive spirit, fed too by its role as a strategic naval base during the Second World War and the Cold War (it was crucial during the Cuban Missile Crisis in 1962, given how close it is to the island).
One of the most colorful episodes in Key West's recent history happened in 1982. Faced with a road and immigration checkpoint set up by the U.S. Border Patrol at the only land access to the Keys (supposedly to look for undocumented immigrants and drugs), which caused enormous traffic jams and badly damaged tourism, the mayor of Key West and a group of residents answered with humor and defiance: they declared the island's symbolic 'secession' as the Conch Republic, raised their own flag, named a 'prime minister' and, right afterward, 'surrendered' to the United States, asking for humanitarian aid as a defeated foreign country. The gesture, half political protest and half theatrical joke, achieved its aim: the border checkpoint was removed, and ever since the Conch Republic has been celebrated every year with a festival and remains an emblem of the island's rebellious, ironic character, with its motto 'We Seceded Where Others Failed'.
Since the late 20th century, Key West also established itself as one of the great LGBTQ+ destinations in the United States, with an open, well-established community and social scene dating from the 1970s and 1980s, largely tied to its bohemian tradition of tolerance. That openness, added to the literary legacy of Hemingway and other writers, the fame of its sunsets at Mallory Square and the boom in cruise ships calling at the island, finished shaping contemporary Key West: an economy centered almost entirely on tourism, receiving several million visitors a year.
Today Key West combines its inheritance of shipwrecks, cigars and literature with the challenges of a mass destination on a small, low-lying island: managing tourism, the cost of living that has shot up for its residents and its vulnerability to hurricanes and rising sea levels are the big issues of its present. Even so, it keeps intact the spirit summed up in its local philosophy, 'One Human Family', and remains, ninety miles north of Cuba, one of the most singular corners in all of the United States.